


Cinderella Saturdays

by Trista_zevkia



Category: Supernatural
Genre: Alternate Universe - Modern Setting, Alternate Universe- No Supernatural, Coming Out, First Meetings, M/M
Language: English
Status: Completed
Published: 2016-03-28
Updated: 2016-03-28
Packaged: 2018-05-29 14:04:23
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,742
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6379015
Author URL: https://archiveofourown.org/users/Trista_zevkia/pseuds/Trista_zevkia
Summary: <blockquote class="userstuff">
              <p>An old prompt, that I don't know where I saw it, about Dean not realizing that Sam knew he was bisexual until Sam sets him up with Cas.</p>
            </blockquote>





	Cinderella Saturdays

Zachariah was in charge of public relations and marketing for a very large firm. Sam was kind of surprised whenever he remembered this, because Zach was a jackass who had no idea what people actually wanted or considered acceptable. If he did, he'd know that Sam didn't want to "dialogue" with him, or do him a favor. In short, Zachariah was an asshat, but that wasn't Novak's fault. Being new to the office and generally low man on the totem pole, no matter how good his grades had been, Sam had to smile and agree with Zach. Instead of bowing out because of his plans, Sam had to smiled and lie.

"Of course I'll entertain Mr. Novak for the evening." 

As if he didn't trust Sam, Zachariah made sure to escort them both out of the building, chatting with them until his driver picked him up. Finally, in the soft, spring night, Sam got a chance to actually turn and speak directly to Mr. Novak. 

"If you don't mind walking, the restaurant I have reservations for is just a block over." 

"I'd prefer to walk." 

Even though he didn't smell of cigarettes, Novak must have smoke two packs a day to get that gravel in his voice. Sam thought that, but he didn't say it, as he wasn't Dean. And, it was time to explain about Dean. 

"Mr. Novak, once a month, I meet my brother for supper at this restaurant for Cinderella Saturdays." Sam could have face-palmed at himself, as now he had to explain that. 

"It's just a nickname for our meetings, it doesn't mean anything. Well, it kind of does, see, we had a weird childhood. Moved around all the time, and my brother, Dean, practically raised me, while going to school and working. He likes things neat and homey, but he was so busy trying to be an adult that he came up with Cinderella Saturdays. I'd do my homework Friday night, and all day Saturday we'd clean whatever apartment or motel we were living in that week, go to the laundromat, buy groceries. Sometimes he had to work, but when he could; we'd shower and put on our nicest clothes, and go out for the best meal we could afford. Like Cinderella going to the ball." 

Novak made an interested noise, but didn't comment. Sam felt he had to fill up the silence, since he was supposed to be impressing the VIP, so he talked some more. 

"Dean basically put me through college, after making sure I got the chance to go. I did some things I'm not proud of, which strained our relationship. And when I passed the bar and got this job, already making more money than Dean's ever seen, I almost destroyed our relationship. He saw it as me trying to buy him off or something. It was bad. But, we got through it, sort of, and this is our Cinderella Saturday now. I know it's Wednesday, but he lets me buy him fancy food and beer while we get to know each other as adults." 

Sam stopped outside the restaurant, a small fusion place with a microbrewery. It wasn't really that expensive, not by the standards of anyone else in the firm, but it was about as expensive and exotic as Dean could handle. 

"He's as smart as I am, though he was always too busy making up for Dad's mistakes to care about his schooling. He's a mechanic, and gets kind of down on himself if we go anyplace that's, well, probably more in line with what you're used to." 

With a nod and shrug at Novak, Sam went in. He was probably being rude to Novak, but he really needed to talk to Dean before anybody made a scene. Besides, Novak hadn't tried to talk during the few pauses in what Sam had said, so maybe he didn’t want to talk either. 

The place was kind of busy, so when the hostess saw Sam she smiled, and pointed to his usual table. Nodding and smiling back, Sam went and sat with his back to the door. He wouldn’t be able to see Dean come in, but this would make Dean walk up to the table before demanding an explanation. Sam expected Novak to at least pretend to be interested in the menu, but he sat on the edge of his seat to stare at Sam. His very blue eyes were kind of disconcerting when he was focused on something, or so Sam decided. 

"Mr. Winchester, I am not a socially adept man. I am supposed to be picking a location for a new office for an accounting firm, so all the businesses we work with have been wining and dining me." 

The intense little man made actual finger quotes around wine and dine, and Sam had no idea how to respond to that. 

"They have matched me up with every single woman the company employs and taken me to the most expensive places their expense accounts can afford, which is not how you woo an accountant. Still, this is the first time I have been made to feel as if I am intruding." 

And just like that, Sam saw his nice little life here go up in smoke. But Novak kept talking, before Sam could even form an apology. 

"But I blame the unctuous Zachariah, as he should have taken me out instead of forcing me on you, as you so politely tried to suggest." Novak flicked his eyes away, brought them back to Sam's face, and then back to the door in a classic double take while he talked. His words got slower, even as his eyes followed something Sam wasn't able to see. "I think I can get a cab back to my hotel, after I eat at the bar or wherever I can watch that Adonis swallow." 

Novak blinked several times and turned back to Sam. "Did I stop speaking after I said I'd eat at the bar?" 

The politic thing to do would be to say yes, you didn't say anything about men who swallow. That would let Novak off the hook for kind of outing himself as gay or something the corporate world still frowned on. But, the safest thing might be to use it, to make sure Novak didn't rat him out for not kicking Dean to the curb to show Novak a good time. But one of these actions Dean wouldn't approve of, not without proof that Novak was a bad guy. 

"You don't have to eat at the bar, just let me explain and my brother will be cool with it." 

"I will?" Dean asked, his tone perfectly polite. 

Novak was staring up at Dean with the same dazed and drooling look he'd sent the Adonis. Oh, right, his brother was pretty hot, Sam could admit that, objectively, and never to his jerk-face. Sam stood, and smiled at his desperately single, who thought he was secretly bi, brother. 

"Dean, this is Mr. Novak. As I was leaving work tonight, Zachariah asked me to show him a good time. Since the best times I have are when I'm with you," Sam started, only to be predictably interrupted by Dean's annoyance. 

"Laying it on a little thick, Sammy." Dean rolled his eyes, so Sam rolled his back in response to the nickname. 

"I don't mind sharing you at the occasional dinner." Dean muttered and pulled over a chair to their table. Sam sat back down, and grinned as Dean sat. Dean turned a smile to Novak and held out a hand to shake. 

"Dean, this is Mr. Novak." 

"Castiel Novak." Novak seemed eager for his chance to shake Dean's hand, or touch the Adonis he'd been ogling, Sam wasn't sure which. 

"Nice to meet you, Casti... " Dean trailed off on the unusual name. 

"Castiel, my religious scholar father named me after the Angel of Thursday." Novak said with the air of someone who'd spent a great deal of time in his life explaining that one thing. 

"Angel, huh?" Dean nodded thoughtfully, politely. 

But Sam knew that tone, knew there was a cheesy pick-up line in Dean trying to get out. Angel seems like a good description, or can I be your lost soul, and Sam had to stop trying to delve into the rabbit hole that was his brother's mind. 

"Castiel, Dean is single and bisexual." 

Dean stared at Sam, but didn't speak until three-fourths of his blood was in his face. "Dude, you can't just describe someone that way. You've embarrassed Cas." 

Reaching out, Sam grabbed Dean's chin and forced him to look. Cas (and didn't that little nickname stick quickly) was holding out his phone towards Dean, working up the courage to ask for a phone number. Blushing so that he looked like a ripe pomegranate with little brown spots, Dean looked down. Cas put his phone on the table, a little bit closer to Dean than to himself, a subtle suggestion that had Sam grinning. 

After chugging Sam's water, Dean calmed down enough to ask, shyly, head down and eyes flicking to Sam. "How did you know?" 

"Dean, you're my brother, hell, you stole me my first skin mag. I know what you look like when you're checking someone out, and there were an awful lot of times you were checking someone out without a woman in sight." 

"You're not mad?" 

"I always figured you'd tell me when you were ready, but I had this idea that Cas might be interested in knowing now." 

Cas blushed a little at that, realizing he had mentioned that watching him swallow thing out loud. "Dean, if it makes it any easier, I would like to say I am very much interested in getting to know you better, in any capacity." 

Dean looked up to stare at Cas, licking his bottom lip subconsciously, before looking at Sam. Whatever he saw must have been enough, because he straightened up. His face took on that charming leer that Sam knew so well, and Dean put his number into Cas' phone. Cas grinned back, something predatory in his eyes, and Sam had a moment to wonder just what he'd let himself in for. But, well, if it made Dean happy, it'd be worth it. And he finally realized a good thing about living on opposite sides of the city from his brother; Sam wouldn't have to buy earplugs. 

҉ 

**Author's Note:**

> [Buy Me a Coffee?](https://ko-fi.com/W7W35853)


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